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Improved synthesis and low-temperature performance of a series of saturated α-branched fatty acids

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Abstract

Five saturated α-branched fatty acids, also known as Guerbet acids, including α-propylhexyl acid (G 1 ), α-butylhexyl acid (G 2 ), α-propyloctyl acid (G 3 ), α-butyloctyl acid (G 4 ), and α-hexyloctyl acid (G 5 ), were synthesized in high yields by four-step reaction. Colorless, almost odorless, and oily products were obtained with high purity, whose structures were confirmed by GC, 1H/13C NMR, and ESI–MS characterization. G 1 , G 3 , and G 4 had pour points lower than −60 °C, while G 2 and G 5 showed higher pour points (−42 °C and 6 °C, respectively) because of their molecular symmetry. Considering the low-temperature properties, G 1 , G 3 , G 4 , and even G 2 held great potential applications in the lubricant and oilfield.

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References

  • Browning E, Woodrow HW, Adams R (1930) Preparations and bacteriological action toward B. leprae of certain olefinic acids. J Am Chem Soc 52:1281–1283. doi:10.1021/ja01366a076

    Article  CAS  Google Scholar 

  • Cassani F, Celentano G, Erba E, Pocar D (2004) New synthesis of optically pure a-branched aliphatic carboxylic acids from amidines. Synthesis 7:1041–1046. doi:10.1055/s-2004-822335

    Google Scholar 

  • Denotter MJ (1970a) The dimerization of oleic acid with a montmorillonite catalyst I: important process parameters; some main reactions. Fette Seifen Anstrichmittel 72:667–673. doi:10.1002/lipi.19700720809

    Article  CAS  Google Scholar 

  • Denotter MJ (1970b) The dimerization of oleic acid with a montmorillonite catalyst II: GLC analysis of the monomer; the structure of the dimer; a reaction model. Fette Seifen Anstrichmittel 72:875–883. doi:10.1002/lipi.19700721010

    Article  CAS  Google Scholar 

  • Erdmann N, Wölk C, Schulze I, Janich C, Folz M, Drescher S, Dittrich M, Meister A, Vogel J, Groth T, Dobner B, Langner A (2015) Tris(2-aminoethyl)amine-based a-branched fatty acid amides—synthesis of lipids and comparative study of transfection efficiency of their lipid formulations. Eur J Pharm Biopharm 96:349–362. doi:10.1016/j.ejpb.2015.08.011

    Article  CAS  Google Scholar 

  • Haßelberg J, Behr A (2016) Saturated branched fatty compounds: proven industrial processes and new alternatives. Eur J Lipid Sci Technol 118:36–46. doi:10.1002/ejlt.201500461

    Article  Google Scholar 

  • Hexion (2015) Technical Data Sheet: VersaticTM Acid 10. http://www.hexion.com/products/technicaldatasheet.aspx?id=6018

  • Kent JA (2012) Handbook of industrial chemistry and biotechnology, vol 1. Springer, New York, pp 353–355

    Book  Google Scholar 

  • Kinsman DV, Johnson RW, Fritz E (eds) (1989) Fatty acids in industry. Marcel Dekker, New York, pp 233–276

    Google Scholar 

  • Keenan MJ, Krevalis MA, Kirk R, Othmer D (eds) (2007) Encyclopedia of industrial chemistry, vol. 5, Willy-VCH, New York, pp 27–77

    Google Scholar 

  • Neweck K, Grafahrend W (2012), ullmanns encyclopedia of industrial chemistry, vol 1, no 4. Willy-VCH, Weinheim, pp 117–141. doi:10.1002/14356007

  • Ngo HL, Nuńez A, Lin W, Foglia TA (2007) Zeolite-catalyzed isomerization of oleic acid to branched-chained isomers. Eur J Lipid Sci Technol 108:214–224. doi:10.1002/ejlt.200600246

    Article  Google Scholar 

  • Ngo HL, Dunn RO, Sharma B, Foglia TA (2011) Synthesis and physical properties of isostearic acids and their esters. Eur J Lipid Sci Technol 113:180–188. doi:10.1002/ejlt.201000335

    Article  CAS  Google Scholar 

  • Ngo HL, Yee WC, McAloon AJ, Haas MJ (2012) Process and cost modeling of saturated branched-chained fatty acid isomer production. Ind Eng Chem Res 51:12041–12045. doi:10.1021/ie300451x

    Article  CAS  Google Scholar 

  • Ngo HL, Dunn RO, Hoh E (2013) C18-unsaturated branched-chained fatty acid isomers: characterization and physical properties. Eur J Lipid Sci Technol 115:676–683. doi:10.1002/ejlt.201200323

    Article  CAS  Google Scholar 

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Correspondence to Jiusheng Li.

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Jiang, Y., Hu, W., Xu, J. et al. Improved synthesis and low-temperature performance of a series of saturated α-branched fatty acids. Chem. Pap. 71, 2359–2363 (2017). https://doi.org/10.1007/s11696-017-0230-8

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  • DOI: https://doi.org/10.1007/s11696-017-0230-8

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